Abstract
A sequential one-pot two-step tandem reaction for selective and efficient synthesis of pyrrolo[2,1- a]isoquinoline and its dihydro- and tetrahydro-derivatives has been developed. The tandem reactions of isoquinoline, α-halogenated methylene compounds, aromatic aldehydes, and cyanoacetamide firstly give tetrahydropyrrolo[2,1- a]isoquinolines as main products. The corresponding pyrrolo[2,1- a]isoquinolines and dihydropyrrolo[2,1- a]isoquinolines can be obtained directly by controlling oxidation with DDQ. The mechanism of this tandem reaction involved the 1,3-dipolar cycloaddition of isoquinolinium ylide as the key step. A unique elimination of the amido group preferring to the cyano group has been observed.
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